


A Gamble

by Anonymous



Category: Overwatch (Video Game)
Genre: Alternate Universe - Canon Divergence, Bi-Curiosity, First Time, Multi, Oral Sex, Strip Poker, Vaginal Sex, Voyeurism
Language: English
Status: Completed
Published: 2019-07-31
Updated: 2019-07-31
Packaged: 2020-07-27 16:00:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,010
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20048722
Author URL: https://archiveofourown.org/
Summary: Lena loses a bet to Jesse, but neither she nor Emily are too fussed by it.





	A Gamble

“Read ‘em and weep, ladies,” Jesse says, leaning back in his seat. He grins at Emily and Lena, the last of the Overwatch crew still awake and willing to go up against Jesse McCree’s famous poker skills. In retrospect, they probably should’ve thrown in the towel earlier and saved some face. Emily groans and throws down her cards unhappily. She wiggles out of her panties and tosses them aside. Lena, however, is not so ready to give up. 

“You’ve got to be cheating,” she says. Jesse’s smile spreads wider. He clasps his hands behind his head and Lena can’t help the way her gaze falls on his bare chest. There’s a dusting of hair across his pecs that she finds particularly fascinating - especially the way it trails down his stomach and thickens just before it disappears into the waistband of his pants. 

“I’m a man of honor, Lena,” Jesse says. “I wouldn’t dream of cheatin’ at a game of cards.” 

“One last round, then,” Lena says. “All or nothing.” 

“Lena,” Emily starts to say, then stops. Lena looks at her. Emily gives her a bemused look, but doesn’t say anything more. 

“What? I’ve got nothing left to lose,” Lena says. She looks back at Jesse, an idea starting to take shape in her mind. “If I win, I take everything - your clothes and mine and Emily’s. If I lose…” 

“If you lose…?” Jesse prompts. “You’ve got nothing left to wager.” 

“Well,” Lena says, suddenly feeling her cheeks go hot. “Maybe we could work something out.” 

Jesse raises his eyebrows. 

“Such as?” 

Lena sneaks a look at Emily then looks back at Jesse. She straightens in her seat. 

“If I lose, I’ll give you head,” Lena says finally. Jesse blinks, taken aback. He drops his arms from behind his head and leans forward in his seat, looking between Lena and Emily. 

“Ain’t you two…?” 

“Together, yeah,” Lena says. Jesse looks at Emily. 

“And that don’t bother you?” 

Emily puts up her hands. “Lena’s been curious since she’s heard my stories,” she says. “And I wouldn’t mind the show.” 

“Well I’m not going to lose,” Lena says. Jesse snorts. 

“You haven’t been doing too hot so far,” he points out. Lena smiles. 

“I have a good feeling about this one,” she says. Jesse leans back in his chair again, considering. Lena glances at Emily again. Emily’s eyes are bright, a spark of something mischievous there. It makes something go warm in Lena’s belly. 

“Alright,” Jesse says finally. He reaches for the cards and starts shuffling. “But I ain’t going easy on you.” 

“I wouldn’t want you to,” Lena says. 

It’s an unmitigated disaster. Lena completely over-estimated her ability to cheat at this game - and Jesse either noticed and let it slide, or he cheated right back at her. Either way, Lena loses again. Spectacularly. She’s already lost her panties and now she’s sitting naked in her seat, her heart thumping in her chest. 

“You don’t have to,” Jesse says, sweeping the cards back into a pile. He looks up at her with a friendly smile. “Go through with it, I mean. We could all just go to bed.” 

“Now now, you made a bet,” Emily interjects. Lena nods. 

“You’re right. And I’m a woman of my word,” Lena says. 

“If you’re sure,” Jesse says. 

“I wouldn’t have offered if I wasn’t prepared to follow through,” Lena says. She lifts a hand and runs it through her hair, letting her eyes roam over Jesse’s bare chest again. 

“She’s stubborn, Jesse,” Emily says. “She’s not going to change her mind.” 

“You seem awfully calm about all this,” Jesse says. “You ain’t gonna be the jealous type, are you?” 

“Like I said,” Emily says, the corner of her mouth quirking up. “I’m interested in watching the show.” 

Lena slides down from her seat. The floor is cold but her whole body feels hot and flushed. Jesse watches her shuffle to him on her knees. He pushes his chair out from the table a little bit more, to give Lena room to come in closer. Emily moves her own chair around to get a better view. 

Lena can feel her heart in her throat, the blood rushing in her ears. She’s never done this before, even though she’s day dreamed about it. Emily used to tell her stories about guys she’s hooked up with in the past - about how different it felt from being with a woman, more raw and rough and primal. Lena has only ever been with women and hadn’t ever really considered being with a man until she started to hear Emily’s stories. She thought she ought to try it at least once, some day, and now seems like the perfect opportunity; she’s glad Emily’s here, she’s glad it’s with Jesse. She trusts both of them. 

Lena stops in front of Jesse, kneeling in front of him. Tentatively, she puts her hands on his knees and pushes them apart. 

“You know what you’re doing?” Jesse asks. Lena looks up at him and grins. 

“Not really,” she says brightly. Jesse blinks then chuckles. He lets his legs spread a little wider. 

“Well, there’s a first time for everything.” 

Lena glances back at Emily, who nods encouragingly. Emily is sitting on the edge of her seat, biting her lower lip, her eyes round and wide and completely focused on Lena and Jesse. Lena takes a deep breath and then lifts her hands to Jesse’s fly. She fumbles with the button and zipper for a moment, but then she manages to get it open. Underneath, she realizes Jesse isn’t wearing any underwear. She glances up at Jesse, who, surprisingly, looks a bit sheepish. 

“Never really saw the point of ‘em,” he says. “Just another layer to get in the way, you know?” 

“You mean I only had to win one hand…?” she says. Jesse shrugs, the corner of his mouth quirked up, a twinkle in his eye. 

“You’re real bad at cheatin’, Lena.” 

Lena huffs out a little laugh and pushes Jesse’s fly open further. She reaches in haltingly, her fingers finding the thick shaft of Jesse’s cock. She moves her hand around the base and is surprised by how thick he is, even though he’s not hard. She follows the length of his shaft - and keeps following it. She reaches in until even her wrist has disappeared into Jesse’s pants before she finds the tip of him. She looks up again. 

“Is this… are you…?” 

“What?” 

“It feels… big.” 

“Oh, wow,” Emily says, somewhere to the side. Jesse laughs and rubs a hand over his face. 

“I have been told that I’m well-endowed,” he says. Lena manages to pull his cock out of his pants and finally gets a good look at it, resting there on his thigh. She doesn’t have any frame of reference but it looks big. Really big. She places her hand alongside Jesse’s cock, comparing the size. 

“Start slow,” Emily says suddenly. Lena glances over her shoulder. Emily is gripping the seat of her chair with both hands, her thighs pressed tightly together. “He’s not hard yet. He’s going to get really big.” 

“Oh,” Lena says. She looks back down at her hand and Jesse’s cock. She runs her fingertips down the shaft, following the path of a thick vein. She can’t imagine that it’s going to get bigger than it already is. 

“Use your mouth, Lena,” Emily says. Her words come out breathy, as if she can barely manage to speak. “Kiss it.” 

Lena glances up at Jesse again. He’s watching her intently, his lips parted slightly. When he meets her eyes, the tip of his tongue flicks out to moisten his lips. 

“It won’t bite,” Jesse says. Lena smiles at that. She leans forward and presses her mouth against the tip of Jesse’s cock. 

It’s warm under her lips - firm, not as soft as she was expecting, but not hard either. She thinks suddenly of Emily’s tits, how they yield under her lips, how her nipples harden under her tongue. This is different, but not unpleasantly so. She breathes in his smell - slightly musky - as she drops kisses down along the shaft, following the vein with her lips as she had with her fingertips. Jesse’s cock twitches under her mouth. 

“Your tongue - use your tongue Lena,” Emily says, her voice still sounding slightly breathless. “Taste him.” 

Lena looks back at Emily again. She’s sitting on the edge of her seat, her knees still pressed together, but one hand is between her legs, her palm pressing against the mound of her pussy, the other still gripping the side of the chair. Her mouth is open, the color high on her cheeks. She locks eyes with Lena and nods. 

“Use your tongue,” Emily says again. Lena swallows and nods. She bends her head over Jesse’s cock and, with the tip of her tongue, laps at the tip of him. His skin tastes slightly salty, that musky smell spreading over her tongue. She laps at him again. Jesse’s cock twitches, thickening slightly - she must be doing something right. 

Lena licks at Jesse’s cock, from the tip down the shaft and back up again. She can feel him get harder under her lips - it’s an odd sensation, but she finds that she likes it. She likes being able to tell that she’s doing something right. His cock is no longer resting against his thigh but is beginning to curve upwards, towards his belly button. Lena shuffles even further forward on her knees to follow the curve of his dick. 

“I think he likes that, Lena,” Emily says. Above Lena, Jesse chuckles deep in his chest. 

“Ain’t bad for your first time,” Jesse says. “Those little kitten licks only get a guy so far, though.” 

“Yeah - yeah, put your mouth around him,” Emily says. 

“I don’t know if it’s going to fit,” Lena says. She drags her tongue along the underside of Jesse’s cock in one long stroke. Jesse makes a pleased noise in his chest. He brings his right hand up to her shoulder and cups the back of her neck gently - his hand is warm and heavy, grounding. 

“Just take it slow,” Emily says. “Get him wet. You’re so -” her voice hitches. “- so good with your tongue, Lena.” 

Lena shivers at the hitch in Emily’s voice. She does as she’s told, though, using her tongue all over Jesse’s cock until it’s shiny with her spit. Only then does she try to take the tip of him into her mouth. She wraps her lips around the head, giving him an experimental suck. Jesse’s grip tightens slightly on the back of her neck. 

“Yeah,” Jesse breathes. Lena raises her eyes to watch his face as she tries to take more of him into her mouth. Her lips stretch as she tries to get more of his cock into her mouth. His mouth falls open and she can hear his breathing go a little harsher. Encouraged, Lena tries to push her mouth down further, but it’s difficult to do so and breathe at the same time. She pulls off to suck in a gulp of air. 

“You have to breathe through your nose,” Emily says. Lena looks over her shoulder at her girlfriend and sees Emily’s fingers moving between her legs, rubbing her clit. It sends a lightning bolt right through her. “Breathe through your nose, and loosen your jaw. Then you can - you can take him.” 

Lena shifts to the side so she can watch Emily from the corner of her eye as she leans over Jesse’s cock again. She opens her mouth and takes the tip of him between her lips. Jesse makes a small appreciative noise, his fingers stroking the hair at the back of her neck. Lena concentrates on breathing through her nose and pushes her own head down. The tip of Jesse’s cock passes between her lips and hits the roof of her mouth and keeps going. Lena nearly chokes. 

“Easy,” Jesse says. Lena pulls back slightly to draw a breath and then pushes herself back down. “Easy, no need to rush.” 

Lena shifts and loosens her jaw a little more - and that’s better. Jesse’s cock slides between her lips, stretching her mouth wide, the blunt tip of his dick nearly hitting the back of her throat. Lena pulls back and then plunges back down again, slowly, testing herself. 

“Atta girl,” Jesse murmurs. Lena feels a little thrill go through her at the praise. She slides her mouth down his cock, taking more of him with each stroke. 

“Make it wet,” Emily says breathlessly. Out of the corner of her eye, Lena can see Emily’s fingers moving faster between her legs. She can hear her fingers slipping against the wet folds of her pussy. Lena shudders. She pulls off of Jesse’s cock and lets her spit dribble from her lips. She uses her hand to smear it down Jesse’s shaft. Jesse’s hips twitch under her grip. 

“Yeah, like that,” he says. “Just like that.” 

Lena smiles, suddenly filled with confidence. She wraps her mouth around Jesse’s cock and starts bobbing up and down in earnest. She can’t take the whole thing in her mouth - he’s too big, too thick - so she uses her hand to stroke what won’t fit in her mouth. She closes her eyes and makes a little moaning sound. Jesse’s cock twitches between her lips, so she does it again. She keeps her mouth loose and wet, and soon saliva is running down the length of Jesse’s dick. Jesse’s hand on the back of her head guides her down gently but firmly. She can hear his breathing pick up now. His cock is so hard between her lips, it’s the strangest feeling, but not unpleasant. Lena keeps at it, encouraged by Jesse’s soft moans. 

“Lena,” Emily breathes. “Oh Lena, look at you -” 

Lena shivers happily. She looks up at Jesse with round eyes, her jaw aching. Jesse meets her eyes, his own mouth hanging open, the color high on his cheeks. 

“I’m gonna - fuck, you feel so good -” Jesse pants. His hand tightens in her hair. His hips jerk under her, and Lena nearly chokes again. “Fuck - I’m gonna -” 

“Lena, he’s going to -” 

“Oh - fuck - !” 

Lena doesn’t have time to react. She feels Jesse’s cock twitch in her mouth and then suddenly her mouth is full of something salty and bitter. He groans as he comes, and he just keeps coming - it feels like it goes on forever. Lena gasps and pulls away, Jesse’s cock spurting over her tongue, her lips, dribbling down her chin. More of it hits her chest, running down the space between her tits. It’s hot and sticky and Lena can’t believe how much there is. Jesse is still moaning even as his cock gives a few final pulses. 

Emily cries out - a sound that Lena is intimately familiar with. When Lena looks, Emily is doubled over in her seat, her thighs trembling. 

“Y’sure you never done that before?” Jesse asks, breathless. His cock is softening against his hip, a trickle of come running down his abs. Lena licks her lips - the bitter taste of Jesse’s come is so different from the sweet tang of Emily’s pussy. 

“Was it good?” Lena asks. Jesse thumbs some come off of Lena’s chin. 

“You’re a mess,” he says. “Why don’t you get cleaned up, huh?” 

Lena gets up, her legs shaky. Her pussy is dying for attention, but she’s patient enough to know that her turn is coming up. Emily grabs her as she goes by. She pulls Lena down and kisses her deeply, sharing the taste of Jesse’s come. Emily moans into Lena’s mouth. 

“Hurry back,” Emily breathes. Lena shudders and nods. She scampers into the bathroom. 

In the mirror, Lena’s reflection stares back at her; flushed, wide-eyed, come spattered. It’s obscene the way it clings to her skin, white globs painting her lips and face. Lena drags a finger through some of the come that’s about to dribble off her chin. She rubs it between her thumb and forefinger, watching it stretch. After a moment, she sucks her fingers clean. 

Lena takes her time cleaning herself up, playing with the come that’s rapidly cooling on her skin. It’s so foreign and weird, and Lena keeps pausing to taste it until it’s mostly gone. 

A noise in the room behind her suddenly draws Lena’s attention. She peeks back out of the bathroom to see Emily bent over the poker table, her legs trembling. Jesse steps forward, his cock hard again, somehow. As Lena watches, Jesse steps forward and rubs his cock against Emily’s ass. She arches and presses back but Jesse puts his metal hand on her hip and steadies her. Jesse sinks into her easily. Emily arches up and cries out. Jesse makes a pleased noise as he thrusts into the hilt. 

“God, you’re so fuckin’ wet,” Jesse mutters. He pulls back and Lena can see the slick glistening on Jesse’s dick. He plunges into Emily again. She yelps. “Yeah, you take my dick real good. Fuck. Look at you.” 

Emily shoves her hips back to meet Jesse thrust for thrust. She works an arm underneath her to get her fingers on her pussy, and she rubs herself hard in time to Jesse’s rhythm. She’s moaning like Lena’s never heard her before - it’s so much more rough than she’s used to. Lena kind of loves it. 

Jesse hunches over Emily’s back, his fingers digging into her flesh. 

“You wanna come on my dick?” Jesse asks. Emily moans. 

“Yes - yes, please - make me come,” Emily says. Jesse reaches under her and bats her hand out of the way. Lena watches his fingers replace Emily’s, rubbing at her clit with purpose. Emily thrashes even as Jesse holds her in place with his metal hand. 

“Come on, come on then,” Jesse says, lips close to her ear. “Come on my cock - don’t I feel good?” 

Emily nearly screams when she comes, her whole body shaking violently. Jesse keeps fucking her through it, his fingers not stopping rubbing circles over her clit. Emily is practically sobbing, the table the only thing that’s keeping her up. Lena steps out of the bathroom. 

“Can… can I have a turn?” Lena asks, surprised at how tentative she sounds. Emily turns her head to look at Lena. 

“I need to see this,” she says, breathlessly. Jesse steps back and Lena gets a good look at his cock covered in Emily’s juices. Emily scrambles up onto the table and pats the space between her legs. “Lie down, baby. Right here.” 

Lena comes over and hops up onto the table, her heart beating in her throat again. Her pussy is aching for attention - she can feel how wet she is already. She lies back and Emily takes her head in her hands, stroking her hair back from her face. 

“Just relax, baby,” Emily says. “Jesse’ll be real good to you.” 

Jesse steps between her legs. His cock looks even bigger from this angle, somehow. It feels huge, too, when he rubs the tip of it up against her pussy. He’s still slick with Emily’s juices and it just makes Lena more wet. 

“I want to feel it,” Lena says. “Please?” 

“Oh, fuck, that’s hot,” Emily says. 

“She’s askin’ so nicely too,” Jesse says. He holds Lena’s legs apart and starts sinking into Lena’s pussy. She gasps. He’s thick - he’s stretching her open so much more than she’s used to. 

“Oh - oh -” Lena gasps. 

“Too much?” Jesse asks, pausing. 

“Don’t stop!” 

Jesse thrusts all the way in and Lena forgets to breathe. She looks down to see where Jesse is disappearing into her pussy and drags her eyes up his sweat damp chest. He grins down at her. 

“Alright?” he asks. 

“Fuck me,” she says. “Please!” 

Jesse starts fucking her in earnest. Lena gasps. She can practically feel Jesse’s cock in her throat. It feels so good, so different from what she’s used to - she feels like she’s going to split in two. She looks down and she swears she can see his cock bulging in her stomach. Jesse grunts, hunched over her, sweat beading on his forehead. Lena wraps her legs around Jesse’s hips and locks her ankles at the small of his back. It has the effect of drawing him even deeper. Lena isn’t sure how much she can take. 

Emily’s hands leave Lena’s head and then the next thing Lena knows, Emily is lowering herself to Lena’s face. Her pussy, still wet and glistening, is an inch away from Lena’s mouth. Lena arches her neck up and licks out at her. With a pleased noise, Emily lowers herself down the rest of the way, straddling Lena’s face while Jesse pounds into her pussy. Lena licks up into Emily, sloppy. She can barely breathe but it feels amazing. Emily’s pussy slides over her lips and chin, even as Lena tries to hold her in place. It’s too overwhelming for finesse - Lena moans into Emily’s pussy, feeling her juices run down her chin. 

Jesse presses his thumb to Lena’s clit and she nearly jumps off the table. He keeps up the pressure, his hips losing their smooth rhythm and dissolving into jerky, sharp thrusts. Lena cries out, twisting under Jesse’s hands and Emily’s pussy, shuddering as her orgasm builds. She doesn’t know how much longer she’s going to be able to hold on. He flattens his palm against her pussy, grinding against it. Lena is aching, her release building - she knows she’s going to be sore tomorrow and she loves every second of it. 

Emily grinds down on Lena’s face, her gasps of pleasure punctuated by praises and encouragement. She leans forward to capture Jesse’s mouth for a kiss and Lena can feel Jesse’s hips stutter against her own. Lena moans into Emily’s pussy. 

“Fuck,” Jesse gasps. His voice has gone higher, needier - a little whine coming into it. His hips stutter again, he’s shaking and then he’s thrusting all the way in, shoving Lena along the table, making her arch up as he buries himself inside her. Lena’s pussy clenches all around him and her orgasm finally hits her. She cries out, muffled by the soft, wet folds of Emily’s pussy. She feels like she’s shaking apart. Her thighs tremble and contract around Jesse’s hips, holding him in place. She feels his cock twitch inside her and it’s the most peculiar feeling - she feels him pulse, feels the flood of his hot come inside of her. She can feel it fill her up and leak out of her around Jesse’s cock. It’s hot and sticky as it oozes from her pussy, dripping down her ass and pooling on the card table beneath her. The edges of her vision go dark and fuzzy. 

Lena blinks as Emily climbs off of her, a rush of cool air against her face. Her lips feel tingly, almost numb. Emily leans down and kisses Lena, her tongue sweeping into her mouth. Lena breathes out as Emily pulls away. 

“Alright, baby?” Emily asks softly. 

“Uh huh,” Lena says. Her head is still spinning. Between her legs, Jesse steps back. She feels the sudden loss of his girth inside of her, and then the gush of come as it rushes out after him. Lena tries to press her thighs together, to keep it all inside. 

Emily reaches up and drags Jesse in for a kiss. Jesse’s hand comes up to cup her face. Beneath them, Lena watches, still trying to catch her breath. 

“So,” Emily says as Jesse finally pulls away. “Same time next week?” 

Jesse blinks, then laughs. “That can be arranged. What d’you think, Lena?” 

“I think I should lose poker more often,” Lena says, dazedly. Jesse helps her sit up and presses a surprisingly chaste kiss to the corner of her mouth. 

“We could probably skip that part, if you want,” Jesse says. 

“I dunno,” Lena says. “I enjoyed it.” 

Jesse laughs. “Same time next week then.” 


End file.
